Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs

doi:10.1155/2013/907525

. 2013:2013:907525.

doi: 10.1155/2013/907525. Epub 2013 Jan 17.

Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs

Chatrasal Singh Rajput¹, Shiwani Singhal²

Affiliations

¹ Medicinal Chemistry Division, Department of Pharmacology, L.L.R.M. Medical College, Meerut 250002, India ; Jubilant Chemsys Ltd. R & D B-34, Sector 58, Noida 201301, India.
² Medicinal Chemistry Division, Department of Pharmacology, L.L.R.M. Medical College, Meerut 250002, India.

PMID: 26556002
PMCID: PMC4590821
DOI: 10.1155/2013/907525

Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs

Chatrasal Singh Rajput et al. J Pharm (Cairo). 2013.

. 2013:2013:907525.

doi: 10.1155/2013/907525. Epub 2013 Jan 17.

Authors

Chatrasal Singh Rajput¹, Shiwani Singhal²

Affiliations

¹ Medicinal Chemistry Division, Department of Pharmacology, L.L.R.M. Medical College, Meerut 250002, India ; Jubilant Chemsys Ltd. R & D B-34, Sector 58, Noida 201301, India.
² Medicinal Chemistry Division, Department of Pharmacology, L.L.R.M. Medical College, Meerut 250002, India.

PMID: 26556002
PMCID: PMC4590821
DOI: 10.1155/2013/907525

Abstract

A series of 3-[2'-(Substitutedbenzylideneamino)phenyl]-2-methyl-6-substituted quinazolin-4-ones (5-10), 3-[2'-(3(″)-chloro-2(″)-oxo-4(″)-substitutedphenylazetidin-1(″)-yl)phenyl]-2-methyl-6-substitutedquinazolin-4-ones (11-16), and 3-[2'-(2(″)-substitutedphenyl-4(″)-oxo-1(″),3(″)-thiazolidin-3(″)-yl)phentl]-2-methyl-6-substitutedquinazolin-4-ones (17-22) have been synthesized in the present study. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, (1)H NMR, and mass spectral data. All the newly synthesized compounds were screened for anti-inflammatory and analgesic activities.

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References

1. Kumar A., Sharma S., Archana, et al. Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors. Bioorganic and Medicinal Chemistry. 2003;11(23):5293–5299. doi: 10.1016/S0968-0896(03)00501-7. - DOI - PubMed
1. Maggio B., Daidone G., Raffa D., et al. Synthesis and pharmacological study of ethyl 1-methyl-5-(substituted 3,4-dihydro-4-oxoquinazolin-3-yl)-1H-pyrazole-4-acetates. European Journal of Medicinal Chemistry. 2001;36(9):737–742. doi: 10.1016/S0223-5234(01)01259-4. - DOI - PubMed
1. Giri R. S., Thaker H. M., Giordano T., et al. Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents. European Journal of Medicinal Chemistry. 2009;44(5):2184–2189. doi: 10.1016/j.ejmech.2008.10.031. - DOI - PubMed
1. Manivannan E., Chaturvedi S. C. Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents. Bioorganic and Medicinal Chemistry. 2011;19(15):4520–4528. doi: 10.1016/j.bmc.2011.06.019. - DOI - PubMed
1. Kumar A., Rajput C. S., Bhati S. K. Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent. Bioorganic and Medicinal Chemistry. 2007;15(8):3089–3096. doi: 10.1016/j.bmc.2007.01.042. - DOI - PubMed

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[1] Kumar A., Sharma S., Archana, et al. Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors. Bioorganic and Medicinal Chemistry. 2003;11(23):5293–5299. doi: 10.1016/S0968-0896(03)00501-7. - DOI - PubMed

[2] Kumar A., Sharma S., Archana, et al. Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors. Bioorganic and Medicinal Chemistry. 2003;11(23):5293–5299. doi: 10.1016/S0968-0896(03)00501-7. - DOI - PubMed

[3] Maggio B., Daidone G., Raffa D., et al. Synthesis and pharmacological study of ethyl 1-methyl-5-(substituted 3,4-dihydro-4-oxoquinazolin-3-yl)-1H-pyrazole-4-acetates. European Journal of Medicinal Chemistry. 2001;36(9):737–742. doi: 10.1016/S0223-5234(01)01259-4. - DOI - PubMed

[4] Maggio B., Daidone G., Raffa D., et al. Synthesis and pharmacological study of ethyl 1-methyl-5-(substituted 3,4-dihydro-4-oxoquinazolin-3-yl)-1H-pyrazole-4-acetates. European Journal of Medicinal Chemistry. 2001;36(9):737–742. doi: 10.1016/S0223-5234(01)01259-4. - DOI - PubMed

[5] Giri R. S., Thaker H. M., Giordano T., et al. Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents. European Journal of Medicinal Chemistry. 2009;44(5):2184–2189. doi: 10.1016/j.ejmech.2008.10.031. - DOI - PubMed

[6] Giri R. S., Thaker H. M., Giordano T., et al. Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents. European Journal of Medicinal Chemistry. 2009;44(5):2184–2189. doi: 10.1016/j.ejmech.2008.10.031. - DOI - PubMed

[7] Manivannan E., Chaturvedi S. C. Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents. Bioorganic and Medicinal Chemistry. 2011;19(15):4520–4528. doi: 10.1016/j.bmc.2011.06.019. - DOI - PubMed

[8] Manivannan E., Chaturvedi S. C. Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents. Bioorganic and Medicinal Chemistry. 2011;19(15):4520–4528. doi: 10.1016/j.bmc.2011.06.019. - DOI - PubMed

[9] Kumar A., Rajput C. S., Bhati S. K. Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent. Bioorganic and Medicinal Chemistry. 2007;15(8):3089–3096. doi: 10.1016/j.bmc.2007.01.042. - DOI - PubMed

[10] Kumar A., Rajput C. S., Bhati S. K. Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent. Bioorganic and Medicinal Chemistry. 2007;15(8):3089–3096. doi: 10.1016/j.bmc.2007.01.042. - DOI - PubMed

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Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs

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Synthesis, Characterization, and Anti-Inflammatory Activity of Newer Quinazolinone Analogs

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